Water → Atamestane

HRID 275067

Reaction equation

HRID 275067 reaction equation
I[CH:2]1[C@H:19]([CH3:20])[C@@:18]2([CH3:21])[C:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])=[CH:4][C:3]1=[O:23].C(=O)([O-])[O-].[Li+].[Li+].O>CN1CCCC1=O>[CH3:20][C:19]1[C@@:18]2([CH3:21])[C:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])=[CH:4][C:3](=[O:23])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11125Lithium CarbonateHCID 677814542-Iodo-1alpha-methyl-androst-4-ene-3,17-dione2×

Product 1

HCID 57050Atamestane

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

14.9 g of 2-iodo-1α-methyl-androst-4-ene-3,17-dione crude product of example 7 and 4.73 g (64 mmol) of anhydrous lithium carbonate are stirred in 95 ml of N-methyl-pyrrolidone for 1 hour at 130° C. under nitrogen atmosphere. After cooling of the reaction solution it is added to 0.6 1 of water and the product is extracted 3 times with 450 ml of ethyl acetate. The combined ethyl acetate phases are dried on sodium sulfate and then concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent. After concentration by evaporation of the fractions and recrystallization of the substance from ethyl acetate, 6.9 g of 1-methyl-androsta-1,4-diene-3,17-dione (69% of theory over 2 stages relative to 1α-methyl-androst-4-ene-3,17-dione in example 7) of melting point 168°-169° C. is obtained.

Workup

  1. temperatureAfter cooling of the reaction solution it
  2. extractionthe product is extracted 3 times with 450 ml of ethyl acetate
  3. dry with materialThe combined ethyl acetate phases are dried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent
  6. concentrationAfter concentration
  7. customby evaporation of the fractions and recrystallization of the substance from ethyl acetate, 6.9 g of 1-methyl-androsta-1,4-diene-3,17-dione (69% of theory over 2 stages relative to 1α-methyl-androst-4-ene-3,17-dione in example 7) of melting point 168°-169° C.
  8. customis obtained

Sources & evidence

ORD record
ord-5fd1ac819c9b4f98ae03bab12d6e5197
Source dataset
uspto-grants-1995_02
Patent number
US05391778

Linked notes

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